Use this URL to cite or link to this record in EThOS:
Title: Claisen-Sakurai approaches to cyclopentane scaffolds
Author: McAdam, Catherine
ISNI:       0000 0004 5371 4592
Awarding Body: Queen's University Belfast
Current Institution: Queen's University Belfast
Date of Award: 2015
Availability of Full Text:
Full text unavailable from EThOS.
Please contact the current institution’s library for further details.
A general approach to the synthesis of densely functionalised cyclopentenols was developed to circumvent selectivity and functionalization issues often encountered when attempting to access these synthetic intermediates using the methods currently in use. A range existing reactions were expanded upon, culminating in the formation of allyl silane starting materials for an intramolecular Sakurai reaction. The protocol was adapted to grant access to 'three of the four possible diastereoisomers of the cyclopentenol product. Conditions for a combined Claisen-Sakurai reaction were established. Treatment of diaryl ethers under basic conditions was found to lead to selective formation of either the 2- or 3- allylated ketone. Exhaustive mechanistic studies led to the proposal of base mediated isomerisation-Claisen and [2,3]-Wittig-anionic oxy-Cope rearrang~ment cascade sequences
Supervisor: Not available Sponsor: Not available
Qualification Name: Thesis (Ph.D.) Qualification Level: Doctoral
EThOS ID:  DOI: Not available